Why did what I owe increase when a loss was entered?

That depends.  While the documents have been uploaded, review the stock section of TurboTax to ensure that the loss amounts have been entered.  In TurboTax online, investment income/loss are entered in Investments and Savings, and by selecting Stocks, Cryptocurrency, Mutual Funds, Bonds, Other (1099-B).  In TurboTax CD/download, select the Wages & Income tab, then scroll down to Investment Income and select Stocks, Mutual Funds, Bonds...

Until you move through the entire income section, TurboTax may not reflect the most up-to-date tax due or refund amount.   Additionally, if you have already entered other investment losses, you might have already offset the maximum amount of ordinary income.  Investment losses will offset investment gains, plus $3,000 of ordinary income ($1,500 of ordinary income if you file MFJ). 

@333jc 

thank you!  I do understand the limit of $3k of benefit... but I am perplexed that as I entered 2 investment accts with losses why the amount owed went up a little bit?

Capital loss reduces your total income and your taxable income. However, by reducing your income it can reduce some of the credits that you might be getting.